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If there’s one thing every Dating Ninja knows it’s that first impressions are everything in the world of online dating. That first email you send to someone on an online dating site can make or break your chances of getting a response. But with a little thought and little effort you can increase your chances of getting a response.

These are the DO’s and DON’T’s for that first email:

DO personalize the email and mention something from the person’s profile and tie it back to you. For example, I notice you like Green Day. Did you see them when they were in town last year? It was a fantastic show.

Finding love is something millions of people are willing to pay for, even in a recession. Online dating sites like Match.com and eHarmony have taken that fact to the bank, and with the recent success of Patti Stanger’s Millionaire Matchmaker TV show on Bravo, it’s no wonder that ordinary people all over the country have started hanging out a shingle proclaiming themselves to be matchmakers. So I wasn’t surprised a few weeks ago when a friend of mine told me she had recently been to one. However, I was surprised that said matchmaker was right in my own backyard in Lake Oswego, a small suburb of Portland, Oregon.

The only personal experience I have ever had with a “matchmaker” was the intake interview I had with a 20-something sales associate at It’s Just Lunch many years ago. I filled out a form, she briefly interviewed me, and then proceeded to set me up with dates over the next 12 months. Although she did set me up with some pretty interesting men, there was no real coaching or follow up after that initial intake interview. The only real advice she gave me was on what not to talk about on the first date: sex, religion, politics. She set me up and I was on my own.

Enter Jacqueline Nichols, personal matchmaker and proprietor of Intuitive Matchmaking in Lake Oswego. I was very curious about this local matchmaker so I sent her an email and arranged for a visit.

The Intuitive Matchmaking office is located in a small business building nestled in the middle of the First Addition neighborhood in Lake Oswego, and you’d never know it was there if you didn’t know exactly where to find it.

Her office space is intimate and colorful with little reminders of that love her clients are so desperately seeking. I notice a stack of brochures featuring photos of happy couples romping on the beach and the tagline “Find love. Enjoy love. Keep love” printed on the cover. Nichols takes a chair and I seat myself on – what else – but a love seat.

I ask the obvious question, why become a matchmaker?

The answer to that question lies in the name of her business, Intuitive Matchmaking. “I have been doing spiritual work for 25 years, and have been a sort of spiritual life coach for so many people through my Gratitude for Success business,” she explains. “Part of being a spiritual life coach is helping people find balance and joy in all aspects of their life including their relationships, so it was just a natural instinct to help my clients find love as well as success in other parts of their life.” It wasn’t until her clients started writing “matchmaking” in the memo on their checks that the light bulb really went on.

“I match people at the soul level,” she says. “That’s the difference. I pay attention to what chapter of your life you’re in right now and find you someone who’s in that same place.” A lot of her clients come into the service wondering why their relationships aren’t working out. “There’s a big difference between dating material and husband/wife material, and that’s where I can help.”

So what do you get when you hire a matchmaker like Nichols? Well that depends on how much you’re willing to pay. The Beginners membership to her service starts at $99, which gets you a personal consultation and a spot in her database, where you can search to your heart’s content. If you are an Elite member Nichols will proactively search her database for matches and possibly match you with “hidden clients” who are not public in her database. You also get a monthly consultation at this level.

The top level in her service is the Platinum tier. “I am basically your personal on-call matchmaker at this level,” she says. “The Platinum clients have access to me 24/7, and I will search outside my database for matches for them if I need to.” If you have to ask the price you probably can’t afford it.

Although there are no guarantees in the search for love, Nichols claims to have a very high success rate. “I can usually find a match for someone in one to three introductions,” she says. But don’t expect those introductions to all happen in the first week. “I know your time is valuable, and I will not make an introduction unless I know it would be worth your time.”

Her database of clients is small (about 500 people and growing) in comparison to the online dating institutions like Match.com or eHarmony, but consider the fact that Nichols has done her homework on your potential matches up front. “I have met or done a phone consultation with every single person in my service. And I do background checks on everyone as well. It’s all about quality not quantity.”

Although I have never claimed to be a matchmaker I have certainly become the go-to person in my circle of friends when it comes to questions about dating, especially online dating. So, I was extremely curious to hear Nichols’ perspective on the state of dating and courtship in today’s society.

“People don’t know how to date,” she says, and I couldn’t agree more. We both agree that people are very quick to judge someone on a first date, which means in the world of fast-food dating (like Match.com) there are very few second dates. And who’s quicker to judge on a first date? According to Nichols it’s women.

“Men seem to be more forgiving on a first date. If there’s no immediate chemistry they will usually give the woman a second chance just to see if there’s something there. Women on the other hand usually have a much longer check list in their head, and if he doesn’t have that one thing they walk away.”

Nichols says people need to slow down and be more patient, and just allow the other person to get to know you. She suggests to give it at least three dates before you throw in the towel, preferably five. And what’s the perfect first date venue? “Not a coffee date!” she says with a hint of frustration. “A coffee date just says, you’re not really that special, and I want to make sure I can get out of here fast if this date is a disaster.”

In her opinion a better choice would be happy hour (2-drink max), or a meeting at a bakery and then a walk, or just a glass of wine and appetizers somewhere. “You need one to two hours with nothing scheduled after the date, so you don’t feel like you’re constantly looking at your watch because you have to be somewhere else in an hour.”

According to Nichols the biggest mistake people make on a first date is being too full of themselves. “They sit there and talk about themselves the whole time, and never really even take the time to get to know the other person.” She says men and women are equally guilty of this.

My next question is a hotly-debated topic amongst my wide circle of friends.Why do so many older men only want to date younger women? I think I already know the answer to this question, but I want to hear what she has to say.

“I don’t get those men as my clients,” she says. “The successful men in my service are looking for a partner not an accessory. Successful older men who only date younger women are doing so because they think they’re a great catch, even if they’re not.”

And what about the older women? “A lot of them want to date their fantasy,” she says. “They want to date younger men because they are trying to recapture that feeling they had in college when they fell head over heels in love and everything was so fun and easy.They are trying to make up for all of those lost years.” She says a lot of women my age are in that category. “The hardest thing I have to do is tell those women to look in the mirror and be honest with what they see. You may feel younger than you are, but you don’t look like you’re 25.” Oh snap!

Nichols’ business currently focuses on the Portland/Vancouver Metro area, but she plans to expand her business in the near future to reach out to clients in Seattle and Medford. Wait, did you just say Medford? Isn’t the median age in Medford 75? Apparently retirees in their 60s and 70s are looking for love too, and Nichols aims to help them find it.

In the end her advice is pretty straight forward and simple. Stop watching the clock, stop focusing on the finish line and just enjoy the journey. And if you want to hire someone to ride that roller coaster with you hire a matchmaker.

I just got an email from a guy on Match.com who seems really interesting but has no profile picture. Why would someone post an online profile with no photo? Do I hit Delete or answer the email?

Please advise.

Kate, Age 37

Dear Kate,

It is my experience that in the majority of the cases where someone doesn’t post a profile picture it is because they are either married or in a relationship. However, there are actually some very good reasons why some people can’t post photos in their profiles. Some people in high profile jobs or in industries where posting their photo may be a danger to them just can’t take the chance.

Don’t be shy. Just ask. You can start with, hey I notice you don’t have a photo posted. Are you a) Married, b) A public figure, or c) A Member of the WItness Protection Program?

He could be a judge, a school principal, or a prison guard. Or he could be married, in which case you hit the big DELETE and BLOCK button immediately.

I get phone calls and emails all the time from people who run into situations in the online dating arena and need some advice. I’ve decided to start publishing those here so you can all reap the benefit of the answers.

Dear Dating Ninja,

I’ve been exchanging emails with a woman online who has no profile picture, but offered to send a photo via regular email. When I opened the photo I noticed she was wearing a wedding ring. What do I say in this situation?

Sean, Age 47

Dear Sean,

The wedding ring in the picture raises two red flags. One, she may still be married, and she’s online seeing if there are better fish in the sea. Or it’s an old picture. Either one is unacceptable.

Write back to her and say, I noticed you’re wearing a wedding ring in your photo. You said you’ve been divorced for quite some time. Do you have a more recent photo you could share?

In the prehistoric dating world we dated people at work, in the neighborhood, or in the same zip code. If we were really adventurous we might venture to a neighboring zip code for a date. Well online dating has expanded that dating radius to every zip code, area code, postal code and country code in the world.

That’s great, right? Sure, if you have unlimited vacation time and a bottomless bank account.

What happens when a guy in area code 503 (Portland) meets a gal in area 206 (Seattle)? They exchange a few emails, maybe a phone call, and then one of them offers to make the 3-hour drive to meet for coffee (more likely dinner because it’s such a long drive). They meet and immediately realize there’s no chemistry. She thinks he looks 10 years older than his profile picture. He thinks she looks 30 pounds heavier. And they are both right. They could have saved themselves a lot of time and money if they would have done one thing: had a Skype coffee date.

All of the emails and phone calls in the world won’t show you what Skype will. Skype adds the dimension of body language that you can’t get via email or phone. I highly suggest you skip the lengthy emails and phone calls and go straight to Skype.

The First Skype Date

Do yourself a favor and treat the first Skype date like you would any other first date. That is, take a shower, put some clean clothes on, brush your teeth, and pretend you’re actually meeting in person. I suggest “meeting” for coffee first, and following the suggestions below:

Pick an area in your home that is free of clutter, and doesn’t have any personally identifying information in it.

Set your computer on the table facing where you plan to sit, and then walk around to the back of the computer and take a look at what your date will see. Is there some hideous art in the background? Pictures of your kids? Your ex? Take them down or pick another spot.

Check that the light is flattering. Fluorescent lights and overhead spotlights are the worst.

Take a picture of yourself with your webcam so you can see the environment and the lighting before your date.

Make yourself a cup of coffee or tea before the date, and off you go!

The Second Skype Date

If you’re still not quite sure if you want to drive the three hours to meet your date in person, or fly 5000 miles as was the case with my first Skype coffee date, have a second date. In fact, make it a lunch or dinner date. You think I’m kidding? I’m not.

Have you ever been annoyed by the way someone eats a salad, munches their popcorn, or slurps their soup? Yep. Have a date that inlcludes food. Set your laptop on the kitchen table and have a meal with your date.

Once you have had a couple of Skype dates you’ll know if you actually want to make the effort to meet in person. You will also get the added bonus of not having first-date jitters when you have your first real date, because you’ve basically already met.

I am a registered member of a dating site called OKCupid. One of the unique features of the site is you can write Journal entries, which I occasionally do. I posted the entry below a few days ago and I couldn’t believe how defensive some of the guys got. It was like I had personally attacked their masculinity with my simple tips on how to choose the right main profile photo.

Here’s the post:

Okay guys, listen up. I’m going to let you in on a couple of secrets about what goes through the mind of a woman when she looks at your profile and decides whether or not to read it or click the dreaded Hide button.

You have less than five seconds to catch our interest. This is the order in which most woman I know would notice things in your profile:

1. The first thing we look at is your MAIN photo.

2. The second thing is your screen name. Screen names like “PatheticLonelyGuy” and “Just4Sex” say a lot about who you are, how you feel about yourself, and what you’re looking for.

3. The three adjectives.

4. The first sentence in your profile (if we get that far).

Lesson 1: The Profile Picture

This is all about that very first picture we see. The rest of the photos shouldn’t follow all of these suggestions.

These are the DOs for your MAIN profile photo:

1. Headshot that clearly shows you from the shoulders up.

2. Smiling please. No one wants to date a sour puss.

3. Face the camera. No profiles.

4. Make sure the shot is in focus.

5. Recent photo.

6. Look directly into the camera. I realize I violated this with my original profile shot I had up, but there are exceptions to every rule.

These are the DON’Ts:

1. No hats. We want to see your hair or your chrome dome, as the case may be.

2. No sunglasses. We don’t trust you if we can’t see your eyes. How would you feel if you met a woman for a date and she never took off her sunglasses? Would you trust her.

3. Shot of you from far far away. Save that for the second or third photo.

4. No dead animals land or sea. A shot of you in a fishing hat and sunglasses holding up a dead fish does absolutely nothing to ignite the passions in a woman.

5. No photos of yourself in the bathroom. I take self shots a lot, but you’ll never see a bathroom mirror, shower stall or toilet in the background!

I recently had an experience where I met someone online and then a few days later did some cyber sleuthing only to find out the person was not who they really said they were. I felt a little violated, you know like someone had hacked into my OS and planted a Trojan virus. And this is someone I met only once for coffee!

This experience got me thinking, why can’t I run my dating life like I run my servers (computers) at work?

Opening Ports of Communication

A port on a computer is a communication channel that allows devices to talk to each on the same piece of hardware without interfering with each other. Think of it as a phone number. If you publicize that port number anyone can call it. Don’t publicize your port number unless you’re ready to communicate!

Install Anti-Virus Software

I would never open up a server at work to the outside world without first installing some sort of anti-virus software to protect it. You’ve all heard of computer viruses, those nasty little programs that hackers and spammers secretly install on your poor unsuspecting computer. In the IT world there are anti-virus software programs like McAfee, Norton and Semantic for that.

The anti-virus software in the dating world is called your gut instinct. Just like Norton your gut will raise all kinds of red flags when it senses danger. Would you ignore Norton if it popped up a message that said some malicious piece of code was trying to gain access to your computer? I think not. You would click that Quarantine or Delete button without a second thought.

So, the next time you’re on a date, and that anti-virus gut instinct software starts popping up messages, don’t ignore them! Hit that Delete button and run!

Whitelisting

My production servers at work are locked down tighter than Alcatraz in the 60’s, unless you’re a really good swimmer/hacker. I employ something called whitelisting, which means you can’t talk to my servers unless I know who you are. This is a difficult concept to apply in the dating world, but it can be done. Before you decide to meet that person on Match.com for a cup of coffee talk to all of your friends who have been active in the online dating world. Ask them if they have come across this person before. The dating pool is small. The likelihood is that someone you know has already met this person for a date, and can give you some very valuable feedback. Positive Feedback=Whitelisting. Proceed with coffee date.

Blacklisting

In the Microsoft world you can blacklist a website by adding it to your hosts file. The hosts file is like a guest list that meaty bouncer outside the coolest club in town has on his clipboard. Not the V.I.P. list, but the OTHER list. You know, the one that lists all the people who have been kicked out of the club at one time or another, and are banned for life. That my friends is the blacklist, and you need one.

While whitelisting is the “known good” list, blacklisting is the “known bad” list. When you log on to Match.com and come across people you work with, add them to your blacklist. Just block them. You know you’ll never date them, and do you really want them perusing your dating profile while they’re deciding whether or not to promote you? And furthermore, blacklist the people you met on Match.com three years ago. The second or third time is not the charm.

Security Certification Process

Many of the clients I work with on a daily basis require my company and my servers to pass a rigorous security clearance. The process involves a lengthy verbal interrogation and a cyber scan of my servers from the outside world to see what they can see. In a word, they are trying to find out that I am safe to communicate with, and that I am who I say I am.

Thanks to the World Wide Web this concept maps very well to the dating world. Most people give you enough information in their dating profile and their initial communications for you to find out more than you ever wanted to know about that person. If all you have is a first name and a city, you may be hard pressed to find any useful information unless the first name is really unique. However, if you have a first name, a city and an occupation you may be in luck. Plug that information into our good friend Google and you’re off and running. You can often find the very pictures they have posted on their dating profile on their business website, which allows you to verify who they are.

If you have an email address or a first and last name and a city, I suggest you get familiar with a site called pipl.com, which takes the information you input and then crawls the Web for you. Pipl.com provides a comprehensive list of all references to that individual anywhere on the Web.

For the serious cyber sleuth I recommend a service called BeenVerified.com, which will give you a 7-day trial if you really need to do a deep dive on someone. This service provides past addresses, name changes, MARITAL STATUS, and criminal records. Don’t ask if you don’t want to know.

Proceed with Caution

People are not as black and white as computers, so even if you employ all of the above methods as you navigate the murky waters of the online dating world, you still need to proceed with caution. Think like an IT manager:

Don’t open a port of communication unless you’re ready for that person to start calling you and texting you. You can always close a port on a computer when you want to stop communicating. In the dating world it’s called blocking his/her phone number!

Don’t whitelist someone until you really know them. Whitelisting someone gives them access to things that no one else has access to.

Do your due diligence, and if you find some compromising information on someone ask them about it before judging them. Not all computer programs are flawless, and not everyone who looks like a criminal online is actually a criminal today.

Go forth young grasshopper, and apply these Dating Ninja skills the next time you decide to try online dating.